Acetic Acid → 2-(4-Chloro-phenyl)-3-cyclopropylmethoxy-pyridine 1-oxide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][CH2:15][CH:16]3[CH2:18][CH2:17]3)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.C(O)(=[O:21])C>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][CH2:15][CH:16]3[CH2:17][CH2:18]3)=[CH:12][CH:11]=[CH:10][N+:9]=2[O-:21])=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 5 g 2-(4-chloro-phenyl)-3-cyclopropylmethoxy-pyridine in 15 mL acetic acid, 3 mL hydrogenperoxyde (30% in water) was added. The reaction mixture was then stirred at 70° C. for 15 h. The reaction mixture was diluted with water and quenched with sodium carbonate. The mixture was washed with methylene chloride. The organic phase was washed with water; then dried over MgSO4 and purified by chromatography on silica gel with a gradient of ethyl acetate to ethyl acetate:methanol 4:1 to yield 3.46 g (65.19%) of the title compound as white solid, MS 276.1 (M+H)+.
Workup
- customquenched with sodium carbonate
- washThe mixture was washed with methylene chloride
- washThe organic phase was washed with water
- dry with materialthen dried over MgSO4
- custompurified by chromatography on silica gel with a gradient of ethyl acetate to ethyl acetate:methanol 4:1
Sources & evidence
- ORD record
- ord-cb7af9e35adc49a9ac1abc79f0afd22f
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090599B2
Reaction notes
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